Why this home stands out
What sets 3304 Winchester Drive apart is its rare dual-base proximity — both Naval Medical Center Portsmouth and Norfolk Naval Shipyard are a five-minute drive away, which is genuinely hard to beat in this price tier. Add a Walmart Supercenter, Chipotle, Dunkin', and Starbucks all within a third of a mile, and daily errands practically take care of themselves. Four bedrooms in a 1941-era home means character with real usable space.
WESTHAVEN PARK and the Portsmouth real estate market
Winchester Drive sits in a mature residential pocket of Portsmouth, Virginia — a city with deep military roots, a revitalized downtown waterfront, and a no-nonsense, community-first personality. The streets here are lined with mid-century homes that have aged into established, tree-shaded blocks where neighbors tend to stick around. Portsmouth occupies the southern bank of the Elizabeth River, directly across from Norfolk, giving residents easy access to two major metro job centers without paying big-city prices for it. The city is home to some of Hampton Roads' most storied institutions, and the presence of both Naval Medical Center Portsmouth and Norfolk Naval Shipyard gives the broader area a steady, service-oriented rhythm. Whether you're commuting in uniform or heading downtown to catch a show at the Commodore Theatre, Portsmouth rewards people who value authenticity over flash. The 3304 Winchester Drive neighborhood specifically benefits from walkable retail, nearby green space, and quick on-ramp access to I-264 for regional travel.
What's nearby
Everyday life runs smoothly from this address. The Walmart Supercenter is 0.3 miles away — close enough to make a quick run feel effortless. For a fast bite, Chipotle Mexican Grill, Taco Bell, and Dunkin' are all within 0.2 miles. Coffee is covered by both Dunkin' and Starbucks Coffee Company, plus a Wawa just 0.3 miles out. If you want to stay active, Sports Performance House and Zenya Yoga Studio & Yoga Academy offer two very different approaches to fitness, both within 0.3 miles. Green space is accessible too — Seaboard Square is 0.4 miles away, with Maplewood Park and Kinley Park rounding out your options within a mile.
For different buyers
For military families relocating
Five minutes to Naval Medical Center Portsmouth and five minutes to Norfolk Naval Shipyard — that kind of dual-base access is rare and genuinely valuable for military households managing unpredictable schedules. Four bedrooms give growing families room to breathe, and a VA loan can make the path to ownership here more straightforward than many expect. Portsmouth's military community is large and welcoming, so you'll likely already know someone on the block.
For first-time buyers
If you're stepping into homeownership for the first time, 3304 Winchester Drive offers a low-friction entry point. Four bedrooms give you flexibility — a home office, a guest room, or space for a growing household. The walkable retail corridor means you won't feel car-dependent for daily needs. And with a VA loan potentially in play, the financial picture can look very different than you might assume. This is the kind of home that lets you start building equity without overextending.
More buyer questions
How far is 3304 Winchester Drive from Naval Medical Center Portsmouth?
Naval Medical Center Portsmouth is approximately a five-minute drive from 3304 Winchester Drive, making it one of the closest residential options to the base in the area.
How far is 3304 Winchester Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is also about five minutes away, so households with personnel at either installation can realistically commute without significant drive time.
What is the flood zone status for 3304 Winchester Drive?
Flood zone information for this address is displayed in the FloodRisk tile on this page — check there for the current FEMA designation and any insurance implications.
Is there a garage or off-street parking at 3304 Winchester Drive?
Parking details for this property are best confirmed through current listing documents or a direct walkthrough, as configurations on mid-century Portsmouth homes vary by lot.
Does 3304 Winchester Drive have an HOA?
This property does not appear to be part of a mandatory HOA, though buyers should verify through title review and any applicable city records prior to closing.
Tom and Dariya Milan at LPT Realty know Portsmouth inside and out — reach out to get your questions answered and schedule a walkthrough of 3304 Winchester Drive.
